1. Field of the Invention
The present invention relates to the bioconversion of benzocyclobutene (BCB) to the 3,4-cis-dihydrodiol compound and the subsequent acid-catalyzed dehydration to form the 4-hydroxybenzocyclobutene compound. These novel compounds have utility as intermediates for the production of polymers.
2. Description of the Related Art
Formation of cis-dihydrodiols from various aromatic hydrocarbons by bacteria has been described by D. T. Gibson et al., Biochemistry, Vol. 9, No. 7, 1973, p. 1626.sup.+ and p. 1631.sup.+, and Vol. 12, No. 8, 1973, p. 1520.sup.+. A cis-dihydrodiol intermediate has been found to be a common metabolite in the bacterial degradation of a variety of aromatic hydrocarbons, including benzene, toluene, naphthalene, biphenyl, ethylbenzene, benzoic acid, phthalic acid, anthracene and phenanthrene. U.S. Pat. No. 4,508,822 discloses the preparation of dihydrodiols of the general formula: ##STR1## where R and R' are substituents which may be the same or different, such as halogen, alkyl and the like. Generally, such dihydrodiols are of the 2,3-dihydrodiol configuration. That is, the hydroxy groups are introduced directly adjacent to the ring substituent R. The only known exception to this general rule is the 4,5-dihydrodiol formed by some bacteria in the degradation of phthalic acid.
U.S. Pat. No. 4,520,103 describes the formation of the 2,3-dihydrodiol of indole as an intermediate in the production of indigo.